The present invention deals with the composition, and application of novel quaternary compounds, as softening, anti-tangle, and conditioning agents for use in personal care, textile and related applications. The properties of these novel quaternary compounds which makes them well suited for these applications is the fact that they are substantive to fibers, hair and skin and also very mild to the skin and eyes.
Standard quaternary compounds are prepared by quaternization of a tertiary amine with such agents as benzyl chloride or di-methyl sulfate or di-ethyl sulfate or methyl chloride. These materials are relatively inexpensive but offer several key disadvantages. These include yellowing of fabrics, a tendency to build-up upon repeated treatment, and variability in hand (i.e. softness and feel). Standard softeners used are selected from the following classes:
Class #1. Alkyl Imidazoline Quaternary Compounds made from the quaternization of an imidazoline made by reacting diethylenetriamine, and a high molecular weight fatty acid such as stearic acid. The standard quaternizating agents are di-ethyl sulfate, or methyl chloride, or di-methyl sulfate, or methyl chloride or benzyl chloride.
Class #2. Alkyl or dialkyl tertiary amines quaternized with benzyl chloride or di-ethyl sulfate or methyl chloride or di-methyl sulfate
Class #3. Quaternary compounds of ethoxylated, propoxylated or nonalkoxylated amido amines derived from the reaction of a high molecular weight fatty acid like stearic acid and a polyamine like diethylene triamine. The standard quaternizating agents are di-ethyl sulfate or di-methyl sulfate or methyl chloride or benzyl chloride.
Class #4. Amido amine salts derived from partially acid neutralized amines.
It is known that under certain catalytic conditions, epichlorohydrin reacts with certain alcohols to give an intermediate which can be used to react with tertiary amines to quaternary compounds, U.S. Pat. No. 3,445,440 to Susi (May 1969) and U.S. Pat. No. 3,517,045 to Susi (June 1970) teaches the use of chlorohydroxypropyl ether to alkylate specific tertiary amines which are the reaction product of a primary fatty amine and ethylene or propylene oxide to give compounds conforming to the following structure; ##STR2##
The above compounds are used as antistatic agents in polymeric compositions such as polyolefin. The antistatic properties of these compounds are achieved by the minimization of static charges on the polymer surface. These anti-static materials are incorporated into the polymer melt and are effective by virtue of their insolubility in the molten polymer. The quaternary compounds migrate to the polymer surface and are effective antistatic agents.
U.S. Pat. No. 4,144,122 to Emanuelsson issued Mar. 13, 1979 teaches that tallow alcohol and certain other higher molecular weight non-guerbet alcohols and their alkoxylates can be reacted with epichlorohydrin, then subsequently with tertiary amines to give compounds suitable for paper debonding.
U.S. Pat. No. 4,215,064 to Lindemann et al issued July 29, 1980 teaches that phosphobetaines can be prepared by the reaction of a phosphate or phosphite salt with epichlorohydrin under aqueous conditions. U.S. Pat. No. 4,283,541 to Shroff et al, issued Aug. 11, 1981 teaches the process for the preparation of the phosphobetaines described in Lindemann (4,215,064). None of these patents teach the compounds of the present invention.
A surprising feature of the compounds of the present invention is their liquid nature and mild nature to skin and eye. This makes the materials of the present invention very useful in personal care products. It is the use of guerbet alcohols with their unique branching and the alkoxylates of the guerbet alcohols that results in these highly desirable properties. Neither the Susi nor the Emanuelsson patents make use of guerbet alcohols nor their alkoxylates. Nor are the low irritation properties or liquidity expected from the teachings of the Susi patents or the Emanuelsson patent.
It is the object of this invention to produce high molecular weight quaternary compounds that have improved liquidity and are free of the undesirable by-products found in the more irritating standard quaternary compounds. This improved performance and retained liquidity relates to the fact that guerbet alcohols, with their specific branching pattern allows for the use of a high molecular weight hydrophobe which is less likely to irritate. The use of guerbets through the reaction of that alcohol with ethylene oxide and/or propylene oxide, and the reaction with epichlorohydrin to give a hydroxypropyl linkage, results in the desired high molecular weight quaternary compounds of this invention.
The references cited herein are incorporated by reference to the extent applicable. Ratios and percentages are by weight and temperatures are Celsius unless otherwise stated.